He might just get his wish.
NFL Network Insider Ian Rapoport reported Tuesday that Tampa is planning "to make a strong push" for Jackson, according to a source.
"I've met him before, and we want DeSean. You better believe we want DeSean here," Winston said in February, per the Tampa Bay Times. "I think he would be a great asset to our team. Me growing up an Eagles fan, seeing what he did for the Eagles and back in his Cal days and even with the Redskins, I would love to have DeSean."
The 30-year-old Jackson can still play, leading the NFL last season in yards per catch (17.9) while racking up his fifth career 1,000-yard campaign. He operated as a critical piece in Washington's high-octane offense and would instantly upgrade an already-juicy Bucs attack likely to part ways with 34-year-old receiver Vincent Jackson.
Free agency officially kicks off Thursday, but it's entirely possible we'll know Jackson's future long before then.